Ethyl isothiocyanatoformate → N-(4-t-butoxycarbonylphenyl)-N'-ethoxycarbonyl thiourea

HRID 376542Notes

Reaction equation

HRID 376542 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:15]([O:17][C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH3:16]>C(OC(C)C)(C)C>[C:1]([O:5][C:6]([C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:21]([NH:20][C:18]([O:17][CH2:15][CH3:16])=[O:19])=[S:22])=[CH:11][CH:12]=1)=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl ester

Product 1

HCID 19361546N-(4-t-butoxycarbonylphenyl)-N'-ethoxycarbonyl thioureaYield 96.3%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

In 150 ml of isopropyl ether was dissolved 13.51 g of 4-amino-benzoic acid t-butyl ester. To the solution was added, while stirring at room temperature, 9.83 g of ethoxycarbonyl isothiocyanate. The mixture was stirred for two hours, then the resulting crystalline precipitate was collected by filtration, followed by recrystallization from isopropyl ether to give 21.83 g of the title compound as colorless needles.

Workup

  1. additionTo the solution was added
  2. stirringThe mixture was stirred for two hours
  3. filtrationthe resulting crystalline precipitate was collected by filtration
  4. customfollowed by recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-be98a94639634be3afdafe915ff16868
Source dataset
uspto-grants-2000_02
Patent number
US06020334

Reaction notes

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